In contemporary culture, the term is sometimes used symbolically or metaphorically to refer to the idea that women wish they had a penis, or to refer to anxieties between men about the size of their genitals.

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Sigmund Freud introduced the concept of a little girl's interest in—and envy of—the penis in his 1908 article "On the Sexual Theories of Children," but did not fully develop the idea until substantially later in 1914 when his work On Narcissism was published. It was not mentioned in the first edition of Freud's earlier Three Contributions to the Theory of Sex (1905).

In Freud’s psychosexual development theory, the phallic stage (approximately between the ages of 3.5 and 6) is the first period of development in which the libidinal focus is primarily on the genital area. Prior to this stage, the libido (broadly defined by Freud as the primary motivating energy force within the mind) focuses on other physiological areas. For instance, in the oral stage, in the first 12 to 18 months of life, libidinal needs concentrate on the desire to eat, sleep, suck and bite. The theory suggests that the penis becomes the organ of principal interest to both sexes in the phallic stage. This becomes the catalyst for a series of pivotal events in psychosexual development. These events—known as the Oedipus complex for boys and the Electra complex for girls—result in significantly different outcomes for each gender because of differences in anatomy.

For girls:

Soon after the libidinal shift to the penis, the child develops her first sexual impulses towards her mother.

The girl realizes that she is not physically equipped to have a heterosexual relationship with her mother, as she has a clitoris, labia and vagina, rather than a penis.

She desires a penis, and the power that it represents. This is described as penis envy. She sees the solution as obtaining her father’s penis.

She develops a sexual desire for her father.

The girl blames her mother for her apparent castration (what she sees as punishment by the mother for being attracted to the father) assisting a shift in the focus of her sexual impulses from her mother to her father.

Sexual desire for her father leads to the desire to replace and eliminate her mother.

The girl identifies with her mother so that she might learn to mimic her, and thus replace her.

The child anticipates that both aforementioned desires will incur punishment (by the principle of lex talionis)

The offshoot of these events, often cited in the media and colloquially, is that a girl really wants to become her mother, so that she can control her father.

A similar process occurs in boys of the same age as they pass through the phallic stage of development. The key differences being that the focus of sexual impulses need not switch from mother to father, and that the fear of castration (castration anxiety) remains. The boy desires his mother, and identifies with his father, whom he sees as having the object of his sexual impulses. Furthermore, the boy’s father, being the powerful aggressor of the family unit, is sufficiently menacing that the boy employs the defense mechanism of displacement to shift the object of his sexual desires from his mother to women in general.

Freud thought this series of events occurred prior to the development of a wider sense of sexual identity, and was required for an individual to continue to enter into his or her gender role.

While fashionable for a number of decades, the concept of penis envy is no longer regarded as a serious one by most psychoanalysts.

Although popular in the early twentieth century when the theory was initially floated, Freud’s theories regarding psychosexual development (in particular the phallic stage and the Oedipal crisis) have been entirely discredited[How to reference and link to summary or text]. Theories by other influential psychoanalysts, such as Erik Erikson and Jean Piaget are widely believed to be more broadly accurate and applicable to child psychological development. Having said this, Freud’s theory continues to be relevant in some theoretical circumstances, and is of such historical significance that it continues to find its way into psychoanalytical teachings. Most of Freud's theories are still taught as part of curriculum in almost all universities and academic circles.

A significant number of critics, activists and feminists, have been highly critical of penis envy as a concept and psychoanalysis as a discipline, arguing that the assumptions and approaches of the psychoanalytic project are profoundly patriarchal, anti-feminist, and misogynistic and represent women as broken or deficient men. Karen Horney—a German psychoanalyst who also placed great emphasis on childhood experiences in psychological development—was a particular advocate of this view. She asserted the concept of "womb envy" to challenge the idea of penis envy.

While not the same kind of penis envy as that typically referred to in psychoanalysis, the phrase "penis envy" or "small penis syndrome"[1] is also sometimes used to describe the envy of a male over another male's penis. Although this subconscious or conscious envy may solely be based on the idea that a larger penis is universally more satisfying and appealing to a sexual partner, other implications arise from the fact that a large penis has been seen in many cultures as a symbol of high masculinity, dominance and power. While this whole matter has probably always been a part of human psychology, recent developments have made the issue slightly more public in the western world.
The media attention given to penis size and some women being vocal in their penis size preferences have led some men to state their envy of others with larger penises. Television shows such as Sex and the City and Ally McBeal popularised the penis size issue when characters in these TV shows stated their preference for well-endowed men over more modestly-endowed men. Also, in the 1977 film Annie Hall, Woody Allen's character, upon hearing the question asked by the title character about penis envy, replied that he "was one of the few males that suffered from it." This conception of Freud's theory is usually the explanation behind the term penis envy.

Men can underestimate the size of their own penises, see Perceptions of penis size. Also, there are wide differences between flaccid and erect states which can be misleading as in 'growers' and 'showers.'Grower vs Shower

The media have been criticized for making penis envy into a male body issue equivalent to women's weight (see Cosmopolitan magazine).